Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids

Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids
An-Xin Wu, Jia-Chen Xiang, Shi-Qing Xia, Yan Cheng, Zi-Xuan Wang, Yan-Dong Wu, Miao Wang, Bo-Cheng Tang
A practicable quinoline synthesis from aniline and two amino acids was developed for generating a wide range of quinolines with high efficiency and diversity. Thus, it facilitated the creations of pharmaceutical derivatives, photochemical active compounds, and challenging scaffolds. The concept of using two amino acids as heterocyclic precursors has been raised for the first time. Mechanistic studies revealed that I2 enabled decarboxylation, oxidative deamination, and selective reconstruction of new C–N and C–C bonds processes.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01501

DOI: 10.1021/acs.joc.7b01501

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